The Ten Best THE NANNY Episodes of Season Three

Welcome to a new Sitcom Tuesday! This week, we’re continuing our coverage on the best of The Nanny (1993-1999, CBS), which is currently available on DVD and HBO Max.

The Nanny stars FRAN DRESCHER as Fran, CHARLES SHAUGHNESSY as Mr. Sheffield, DANIEL DAVIS as Niles, LAUREN LANE as C.C., NICHOLLE TOM as Maggie, BENJAMIN SALISBURY as Brighton, and MADELINE ZIMA as Gracie. With RACHEL CHAGALL as Val, ANN GUILBERT as Yetta, and RENÉE TAYLOR as Sylvia.

Season Three sees The Nanny at its funniest and most engaged with weekly narratives that utilize the central couple’s evolving closeness — a vital aspect of this series’ premise. Of course, the year’s collection is NOT free from terrible idea-led gimmicks that represent the worst part of The Nanny’s reputation either (like an entry built around the stunt casting of Elizabeth Taylor, an animated Christmas special, and an on-location cruise ship outing that really offers little by way of character), especially in its latter half. However, Three’s heavy use of the series’ core relationship validates a fundamental tenet of its construction — the idea of Fran as a “proxy wife” to Mr. Sheffield — and by both teasing romance reliably in story and also predicating entire narratives on the possibility of their eventual pairing, the premise is well-invoked (even, as we saw in Season Two, when there are fewer stories about her being a nanny specifically — a fish-out-of-water and “proxy mom”). What’s more, entries that focus on Fran and Mr. Sheffield inherently emphasize their contrasting personas — with the world he comes from juxtaposed against hers, particularly when embodied by her funny family. So, these relationship shows tend to yield great character rewards as well, making them a superb example of situation comedy. Speaking of comedy — this is, again, the show’s funniest year, as it’s taking risks and mostly succeeding because of its situation-based support. And since The Nanny’s raison d’être, more precisely than many sitcoms, is to make us laugh, the fact that this is the funniest year also means that it’s the most self-actualized. Accordingly, if asked to pick a “peak” season of The Nanny, I’d choose Three, for it’s highest on the series’ most important metric (humor) and best features the relational aspect of its premise, which naturally highlights the central characterizations. Plus, with the year ending on a cliffhanger that seems most likely to result in the official Fran/Sheffield pairing, the upcoming premiere’s unbuyable halting of this momentum — all to prolong the inevitable — will prove this to be a height never again reached, for after Three, the show’s credibility with regard to its leads’ rapport, and their own depictions, is harmed. Never again will they be so believable, so funny, and so uniquely present in story.


01) Episode 49: “The Pen Pal” (Aired: 09/11/95)

Fran is nervous when she’s finally going to meet her pen pal.

Written by Jayne Hamil & Rick Shaw | Directed by Dorothy Lyman

Season Three opens with an entry that foretells the year’s focus on building momentum for the likely pairing of Fran and Mr. Sheffield, via a familiar sitcom story about meeting the pen pal — a notion that allows this show to play on the idea that nobody is better suited for Fran than her own boss, with whom she spends an entire evening at a bar (waiting for her mystery man to arrive). It’s simple and unostentatious, but their interactions nobly display their juxtaposing characterizations, and in a narrative framework that reveals the year’s intentions, not to mention this vital aspect of the series’ premise. Additionally, these relationship-led interests also extend to the subplot with Niles and C.C., whose banter gives way to a sexual combustion — the first indication of their eventual endgame romance (which should have fueled more actual story in the back half of this series’ run, primarily when Fran/Sheffield are deliberately sidelined, but I digress…) — and so this whole premiere ends up being a solid showcase for these four regulars.

02) Episode 52: “A Fine Family Feud” (Aired: 10/02/95)

Fran hopes to reconcile her mother and aunt ahead of Maggie’s 16th birthday party.

Written by Frank Lombardi | Directed by Dorothy Lyman

My choice for this season’s Most Valuable Episode (MVE), “A Fine Family Feud” is probably my pick for the series’ funniest, with huge laughs and big beats that nevertheless reveal important elements of the show’s “situation,” utilizing both regular and recurring characters to uproarious success. The story begins as a parenting show where Mr. Sheffield’s idea of the perfect “Sweet Sixteen” party for Maggie is contrasted against Fran’s — it’s a great way to show their intentionally different personas, and in the context of Fran being a proxy mother to Maggie inside of this premise. Then, we meet one of the series’ most amusing peripheral players — Aunt Freida, portrayed with high-hair, bosomy relish by the stellar Lainie Kazan, who is perfect casting, especially when paired with Renée Taylor’s Sylvia, to whom Freida hasn’t spoken in over 15 years. This family drama plays hilariously into our understanding of Fran’s upbringing in Queens and her Jewish heritage — key facets of her characterization that inform her comedy and emphasize how she differs from Mr. Sheffield and his world. And, finally, the main comic centerpiece involves a food fight — a messy climax that indicates the show’s broader comedy, and its willingness to incorporate gaudier notions, particularly here in Season Three, the series’ comedic peak — before ending on a cute Fran/Sheffield moment that reiterates The Nanny’s emotional core, and the guiding focus of this year. So, this installment practices so much of the series’ identity, enabling elements of its premise and some of its best characters to shine — and with a lot of BIG yuks reflective of this peak era as well.

03) Episode 55: “Oy Vey, You’re Gay” (Aired: 10/23/95)

Mr. Sheffield hires a publicist for whom he falls — but she’s attracted to Fran instead.

Written by Eileen O’Hare | Directed by Dorothy Lyman

Dynasty’s Catherine Oxenberg guest stars in this entry as Mr. Sheffield’s new publicist — whom he hires, in large part, to compete with Andrew Lloyd Webber, his rival and one of the running gags about his character that is both unique to his situation and comedically capable of inspiring story beats (if not actual story). However, the real thrust of this offering, as usual, is the premise’s Fran/Sheffield relationship, as the nanny suffers pangs of jealousy over her boss’ crush on his new publicist… that is, until she learns that said publicist is a lesbian more interested in Fran. When treated as a twist, it is a bit of a gimmick, but again, it’s not the thrust of the story, which is instead about spotlighting how right these two leads are for each other… even though it’s still taking them a long time to realize what is already obvious to us.

04) Episode 57: “The Two Mrs. Sheffields” (Aired: 11/13/95)

Mr. Sheffield proposes marriage to Fran, just to spite his visiting mother.

Written by Diane Wilk | Directed by Dorothy Lyman

In Season One, we met Cloris Leachman as Mr. Sheffield’s old nanny — his “proxy mother” — and in Season Three, evidence of the leads’ growing closeness perhaps, we get to meet his actual mother, played by the icy Dina Merrill, who also doesn’t take to Fran. But instead of focusing on the contention between the two women, this script lets Mr. Sheffield drive the action, as he proposes to Fran — though only to spite his mother, whom he knows detests her. This is an idea that would give both lead characters what they want — but for the wrong reasons — so it’s an interesting conflict, and while the centerpiece where Fran (after finding out about Sheffield’s scheme) attempts to discourage him feels a little narratively false (a Lucy plot without the Lucy Ricardo character’s fixed motivation), this narrative itself, with its very explicit use of the series’ core relationship, is enough to make it a popular favorite.

05) Episode 60: “The Kibbutz” (Aired: 12/04/95)

Fran persuades Mr. Sheffield to allow Maggie to go on a kibbutz — but then regrets it.

Written by Frank Lombardi | Directed by Dorothy Lyman

This story is really another parenting show that reveals the differences between Mr. Sheffield and Fran, with a lot of comedy intending to come from the idea of WASP-y Maggie attending a kibbutz in Israel, but the real gold of this half hour — and the reason that I feature it — is the goofy yet absolutely unforgettable flashback sequence to the 1980s, where we get to see Fran, Val, Sylvia, and Yetta (with a glimpse Mr. Sheffield and his crew on TV). It’s a broad set piece, but it’s a bit of a window into their history, with laughs predicated on our understanding of their characterizations. Accordingly, with big yuks coming from the characters in a memorable set piece, this outing made room for itself here. (Virginia Graham appears as herself.)

06) Episode 63: “Fashion Show” (Aired: 01/08/96)

Mr. Sheffield agrees to let Fran design the costumes for a scene he’s producing.

Teleplay by Eileen O’Hare | Story by Eileen O’Hare and Chris Alberghini & Michael Chessler | Directed by Dorothy Lyman

Truthfully, I think this installment boasts a better story in theory than execution, as it’s surprisingly reserved for The Nanny at this point in its run — keeping the comic climax off-screen, instead of boldly showing it and allowing the audience to thrill in its ridiculousness. Now, it’s not uncommon for sitcoms to engage this structure, but The Nanny is a little more obvious with its laughs, so it’s odd that it would pass up the chance to show us a scene from the classic play Our Town where all the actors wear costumes as designed by Fran — whose own eclectic tastes are a fundamental aspect of her characterization, and indeed quite different from the conservative Mr. Sheffield’s. And yet, even if we don’t see it, our understanding of the Fran character carries both the comedy and the conflict, and that’s a testament to how this show has defined her so brilliantly — we don’t even need to see the gag to find it hilarious and unique to her specific depiction. (Fashion designer Todd Oldham appears as himself.)

07) Episode 65: “The Grandmas” (Aired: 01/22/96)

Fran seeks advice from her two grandmas after her mother and father separate.

Written by Caryn Lucas | Directed by Dorothy Lyman

The main draw of this funny half hour is getting to meet Fran’s other grandmother, Grandma Nettie, played by the delightful Marilyn Cooper, who pairs well with the iconic and always reliable Ann Gilbert at Grandma Yetta. With these two on hand, and a story that features a lot of Renée Taylor’s Sylvia, there’s guaranteed to be many laughs, all stemming from their characters — each of whom exists as an extension of Fran. Yes, this story is a little overly convenient and too divorced from the circumstances of the series’ premise, but the subplot takes care of that, as Fran tells Mr. Sheffield he’s too predictable and he tries to prove her wrong — evidence of their growing attraction, and in particular, his affection for her. So, with the relationship, and therefore the premise, invoked on the side, this is a well-rounded excursion.

08) Episode 67: “Love Is A Many Blundered Thing” (Aired: 02/12/96)

Fran assumes that an anonymous Valentine’s note is from Mr. Sheffield.

Written by Dan Amernick & Jay Amernick | Directed by Dorothy Lyman

One of the most overt examples of the central relationship being used to inspire story, this installment provides a potent indication that their pairing should be coming, for it’s crystal clear about Fran’s feelings for Mr. Sheffield, when she receives an anonymous Valentine’s Day note and assumes it’s from him. From there, she decides to publicly announce her feelings to the world by writing him a message back — on a billboard. This enables a physical comedy bit where Fran and Val act in the vein of Lucy and Viv on The Lucy Show (or, to be more era-specific, Cybill and Maryann on Cybill). It’s not the funniest version of this centerpiece ever, but I do have to credit this outing for offering maybe its first deliberate proof that the heretofore mini-Fran named Val actually has a personality — and a source of comedy — all on her own: she’s a ditz. We’ve gotten one-off suggestions before, but never to the point that it’s consistently reflected in her dialogue. For that reason, I wanted to give this entry extra praise.

09) Episode 72: “The Cantor Show” (Aired: 04/29/96)

Fran starts dating the new temple cantor, whom Mr. Sheffield hires for his new show.

Written by Diane Wilk | Directed by Dorothy Lyman

This is another one of the funniest episodes of the entire series, yielding huge laughs via the lovingly caricatured depiction of Fran’s family and their world, taking us to temple with Sylvia and the handsome new cantor (Philip Casnoff) whom she eagerly matches up with Fran. The jokes are fast and furious, and Renée Taylor is in rare form. And fortunately, if the setup seems too disconnected from the Sheffields’ world, the main conflict arises when this cantor gets a job in Maxwell’s show — pulling him away from the church and putting Fran in between her boss and her mother, who is now too embarrassed to show her face in temple. It’s a hilarious Jazz Singer-esque notion that perhaps only this series could successfully parody, based on the established roles of Sylvia, Fran, and Mr. Sheffield. So, with big hahas, and an idea-led plot nevertheless upheld by these characters, this is a primo half hour of The Nanny. (Of note: Burt Bacharach is the cameo du jour, and this was one of two samples for which Renée Taylor earned an Emmy nod. Both she and Fran Drescher were nominated this year.)

10) Episode 75: “A Pup In Paris” (Aired: 05/20/96)

Fran follows Mr. Sheffield to Paris, where they have a romantic time.

Written by Diane Wilk | Directed by Dorothy Lyman

Season Three’s finale is not great — it contrives a way to get Fran in Paris with Mr. Sheffield, where they meet his brother (and Eartha Kitt) and otherwise have a romantic time… But it’s the height of this series’ rom-com “will they/won’t they” tension, for when Mr. Sheffield says “I love you” as their plane starts to go down — some forced jeopardy that we don’t believe, since we know the show is returning — it’s the moment this series has been building towards: when the father tells the proxy mother that she’s more than a proxy, and their pseudo husband/wife dynamic is in fact supported by real, legitimizing feelings. From this point on, because we know that she loves him too and is eager to marry, there is NO GOOD REASON for them not to be together. Accordingly, by ending the year on this note, The Nanny seems to be telling us that next season they will finally be paired. Only, that’s not what ends up happening, and as a result of Four’s labored decision to insist the opposite — going against all of Three’s deliberate momentum — the premise’s core relationship, and the two leads inside it, are no longer a believable investment. With hindsight, that makes this installment a high point that the show will never again reach, for never again will its characters or premise be as effectively utilized within weekly story. And while this outing itself is not great, it represents something greater… especially compared to everything that follows. (Harry Van Gorkum and Tim Bagley also guest.)


Other notable episodes that merit mention include: “Dope Diamond,” which has a terribly contrived episodic story but a fun moment where the three Fine women seek therapy, “Shopaholic,” which boasts a comic idea rooted in the continuity of Fran being jilted by her old fiancé, and both “Your Feets Too Big” and “That’s Mid-Life,” which I only cite for their funny Sylvia beats. Meanwhile, I’ll also shout out gimmicky entries like “Franny And The Professor,” which wastes Michael McKean in a story where Fran goes on Jeopardy! (an easy comic centerpiece with forced motivation), “Val’s Apartment,” which seems mostly like an excuse to wink about Laverne & Shirley via the casting of David L. Lander, “The Unkindest Cut,” which has an amusing narrative setup before it devolves into an on-location Hollywood trip, and “Where’s The Pearls?,” which guest stars Elizabeth Taylor and Rosie O’Donnell in a shamelessly broad half hour that also includes an “amnesia routine” that’s too contrived for even The Nanny in this era. Lastly, it’s not a good one, but I can’t get away without noting “Val’s Boyfriend,” which has two weak stories, but a beloved scene where Fran tries wasabi for the first time and finally clears out her nasal passages.


*** The MVE Award for the Best Episode from Season Three of The Nanny goes to…

“A Fine Family Feud”



Come back next week for Season Four! And stay tuned tomorrow for a new Wildcard!

8 thoughts on “The Ten Best THE NANNY Episodes of Season Three

  1. Thank you for this great review of my favorite season. I think this is “The Nanny” at its funniest and it’s up there with “Frasier” and “Seinfeld” and “Friends” for me this seaosn.

    • Hi, esoteric1234! Thanks for reading and commenting.

      I share your enthusiasm for this season and agree this is the year that it’s most competitive with its era’s best.

    • Hi, BB! Thanks for reading and commenting.

      Glad you enjoyed — stay tuned soon for my thoughts on Season Four!

  2. I cannot stand Fran Drescher so this series has always been a non-starter with me but these past few essays have included some amusing looking episodes. I’m wondering if you think I can enjoy this show despite my reservations for its leading lady?

    • Hi, Martin! Thanks for reading and commenting.

      I think you’ll have to find a way to appreciate how THE NANNY uses Fran Drescher’s partially self-created persona to inform its situation comedy. You don’t necessarily have to love her or the character, but I don’t think you can genuinely enjoy the show without appreciating the way it’s utilized.

  3. I HATE the Elizabeth Taylor episode. I’m sure it’s supposed to be an homage to that Here’s Lucy episode but it’s just ridiculous and not funny. There are more and more episodes like this as the show goes on unfortunately. I still love it though, more good than bad IMO.

    Looking forward to next week!

    • Hi, Elaine! Thanks for reading and commenting.

      Yes, it’s a rough one — not well-rooted in THE NANNY’s “situation” and asking the audience to believe in plot points that stretch the bounds of the series’ aesthetic realism.

Comments are closed.